Reaktion #81665

Reaktionsgleichung

ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonapth-2-yl)ethynyl]benzoate

ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate

Compound 1

ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate

acetic anhydride

p-toluenesulfonic acid

→

title compound

Ethyl 4-[(5-acetoxy-7,8-dihydro-8,8-dimethylnaphth-2-yl)ethynyl]benzoate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   Einengenconcentrated in vacuo to an oil
3. 3
   SonstigePurification by flash chromatography (silica, 10% EtOAc-hexane)

Vorschrift

To 200 mg (0.51 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonapth-2-yl)ethynyl]benzoate (Compound 1) was added 0.13 ml (1.5 mmol) of acetic anhydride and 10 mg (0.05 mmol) of p-toluenesulfonic acid. The mixture was heated at 80° C. for 12 hours, cooled to room temperature and concentrated in vacuo to an oil. Purification by flash chromatography (silica, 10% EtOAc-hexane) yielded the title compound as a light yellow powder.

Quelle